Advertisement

Chemistry of Heterocyclic Compounds

, Volume 10, Issue 9, pp 1060–1064 | Cite as

Lactam acetals

XIII. Ionization constants and spectral properties of N-methyl-2-aryliminolactams
  • V. G. Granik
  • A. M. Zhidkova
  • R. G. Glushkov
  • I. V. Persianova
  • E. M. Peresleni
  • A. P. Engoyan
  • Yu. N. Sheinker
Article
  • 23 Downloads

Abstract

The UV, IR, and PMR spectra of N-methyl-2-aryliminolactams and their salts were examined. The ionization constants of the investigated amidines in aqueous alcohol depend substantially on the ring size (the basicities fall in the order 6 > 7 > 5). On the basis of the correlation dependences of the pK a values of the amidines and the Hammett σ constants it is shown that the π electrons of the benzene ring are conjugated both with the C=N bond and with the p electrons of the exocyclic nitrogen atom. The angles of rotation of the benzene ring with respect to the C=N bond were calculated.

Keywords

Nitrogen Alcohol Acetal Benzene Organic Chemistry 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    N. P. Kostyuchenko, V. G. Granik, A. M. Zhidkova, R. G. Glushkov, and Yu. N. Sheinker, Khim. Geterotsikl. Soedin., 1212 (1974).Google Scholar
  2. 2.
    V. G. Granik, A. M. Zhidkova, T. F. Vlasova, R. G. Glushkov, and Yu. N. Sheinker, Khim. Geterotsikl. Soedin., 533 (1974).Google Scholar
  3. 3.
    R. Huisgen, M. Brade, H. Walz, and G. Glogger, Ber., 90, 1437 (1957).Google Scholar
  4. 4.
    E. M. Peresleni, Yu. N. Sheinker, N. P. Zosimova, and Yu. I. Pomerantsev, Zh. Fiz. Khim., 39, 92 (1965).Google Scholar
  5. 5.
    E. M. Peresleni, V. I. Sheichenko, and Yu. N. Sheinker, Zh. Fiz. Khim., 40, 38 (1966).Google Scholar
  6. 6.
    Z. B. Kiro, Yu. A. Teterin, L. N. Nikolenko, and B. I. Stepanov, Zh. Organ. Khim., 8, 2573 (1972).Google Scholar
  7. 7.
    B. I. Stepanov, B. A. Korolev, and N. A. Rozanel'skaya, Zh. Obshch. Khim., 39, 2105 (1969).Google Scholar
  8. 8.
    B. M. Wepster, in: Advances in Chemistry [Russian translation], Goskhimizdat, Moscow (1961), Chap. 13.Google Scholar
  9. 9.
    H. B. Klevans and I. R. Platt, J. Amer. Chem. Soc., 71, 1714 (1949).Google Scholar
  10. 10.
    K. Maier, M. Baumann, and D. Leuchs, Chemische Zentrallblat, 132, 4525 (1961).Google Scholar
  11. 11.
    V. G. Granik, M. K. Polievktov, and R. G. Glushkov, Zh. Organ. Khim., 7, 1431 (1971).Google Scholar
  12. 12.
    A. Albert and E. Serjeant, Ionization Constants of Acids and Bases, Methuen (1964).Google Scholar

Copyright information

© Plenum Publishing Corporation 1976

Authors and Affiliations

  • V. G. Granik
    • 1
  • A. M. Zhidkova
    • 1
  • R. G. Glushkov
    • 1
  • I. V. Persianova
    • 1
  • E. M. Peresleni
    • 1
  • A. P. Engoyan
    • 1
  • Yu. N. Sheinker
    • 1
  1. 1.S. Ordzhonikidze All-Union Scientific-Research Institute of Pharmaceutical ChemistryMoscow

Personalised recommendations